Real Stories (and Learnings) from the GTM Trenches pt.2
The GTM Newsletter
Currently writing this from the LAX airport lounge after a busy week of meeting portfolio companies and new investors.
If there’s any rap fans who read this, you might find this cool:
I was lucky enough to attend a private listening session for some unreleased tracks from the late Nipsey Hussle and Pimp C this week put on by our friends at Lockerverse.
Of course, I can’t share the new tracks but RIP to Nipsey and this track should give you some motivation to keep pushing on this Friday afternoon:
Keep your eyes on Lockerverse, they are building the cultural hub for Web3 and have some big partnership announcements coming very soon.
But we’re not here to talk about rap, we’re here to talk about scaling tech companies and everything go-to-market.
Let’s get into it.
Real Stories (and Learnings) from the GTM Trenches pt.2
If you’re not following Mark Kosoglow, CRO at Catalyst Software on LinkedIn you are missing a treasure trove of actionable growth advice.
I was lucky enough to work with Mark for four years during my time at Outreach and he’s one of the most talented, thoughtful and hard-working people that I’ve had the pleasure of working with.
And his content game is 🔥 right now.
Here’s a real story from this quarter:
“We started this quarter with a paltry 1.9x pipeline coverage.
In my first full quarter as CRO, I'm not gonna have a miss.
15 days left. What am I doing to hit 110%?
1. Cleaned up pipeline → Rigorous weekly deal reviews. We started in Nov, and by early Dec, we only had real opps in SFDC with accurate ARR, Close Date, Stage, Forecast Category, Risk Assessment, and Next Steps.
The secret...a stage-based sales process with clearly defined exit criteria creates a consistent, coachable methodology for teaching reps how to move buyers through the decision process.
Added benefit...we cleaned up ALL the pipeline, so out-quarter coverage is being managed so we enter Q1 knowing our path to target.
2. Identified must-haves → We identified deals were gonna win. Then, we marked deals we *could* win. This created multiple paths to goal you could literally see.
The secret to must-haves is focus. Take dozens of deals and narrow to a dozen. Be intentional against those deals. Intentionality creates success.
Added benefit...visibility creates confidence. Nothing is better for a company than confident sales reps - they are unstoppable.
3. Started Winter League → We had 2 mtgs/week with reps, leadership, product, success, etc. Reps classify every must-have deal as at bat (mtg today), on deck (mtg tomorrow), in the hole (mtg in 3-5 business days), or not in the lineup (no mtg scheduled). This is a famous meeting I used at Outreach to lock in tough quarters.
The secret...accountability with reps to get in front of buyers. You can make sure the right people are in the right meeting and reps feel prepared. You also create visibility for others to share ideas and help.
An added benefit is as deals are won or lost, you can cycle in other deals which helps everyone see your revenue team can control its business.
4. 20/50/100 → We set pacing goals of 20% to target by end of Nov, 50% end of Dec, and 100% by EoQ. Pacing creates a sense of urgency internally on deals with timelines that can close early. We finished Dec 55% to target by working over the holidays on 2 key deals and the reps on those deals (Alissa Kamhi and Alex Cook) came through for the team!
The secret to pacing is to accelerate a big deal or two to get them out of the way. Having big fish in the boat and off your line creates capacity to work EoQ deals harder.
Added benefit...momentum. The team seeing we are on track makes things fun. Momentum combined with confidence...powerful
5. 2 Week Countdown → We have about 14 deals left that represent 2.2X coverage - awesome for this late in the quarter. 2 of those deals get us to goal. We'll be updating the company almost daily on each deal so everyone is in the know.
The secret is making sure to stay positive and highlight small wins. Keep the momentum building for every mtg booked, strong call, support from other orgs, etc.
Added benefit...clear thinking for #sales leadership. Work daily on deals that matter!”
Check out Mark’s full post with comments here.
📈 How to take action/learnings:
Rigorously clean up your pipeline.
Identify your “must-have” deals.
Start a Winter League (2 mtgs/week with reps, leadership, product, success, etc.).
Follow the 20/50/100 pacing framework.
Start a two week countdown at the end of each quarter.
Enter Juan George, former SVP of Sales at Olo who took them from 0-98M ARR 👀
*click the graphic above for more on his background + a vertical SAAS Playbook*
Here’s one of his favorite stories from that time period:
“CKE Restaurants Holdings, Inc. (“CKE”) runs and operates Carl’s Jr. and Hardee’s, two iconic restaurant brands with nearly 4,000 locations in 40 countries.
In early 2016, they issued an RFP and we lost the deal because the CIO was focused on a Build > Buy despite no proven success around that model. He was fired.
Another CIO came on the board. Granted, this CIO also tried to build a platform at the last company she was at with no success and also didn't select us there.
She decided to continue down the Picks & Shovels Path to Build their Own Olo.
I lived by this quote from the early years (7 to be exact) when our company was trying to find PMF: "Never, ever, ever give up."
We stayed in touch but ultimately knew we "had to let it fail" for them to call us.
By late 2019, 3+ years into the project, they still had no project up & running materially that had got past the pilot phase, had spent millions of dollars, had angry franchisees demanding a solution and a brand that was missing the boat on the hottest trend in the industry: Mobile Order & Pay.
Meanwhile, each one of their competitors sped by them announced their Digital Ordering solutions.
When C-19 hit in 2020, I got a call from that CIO saying her Leadership Team was going to shelve the project and asked if we could step in given the franchisees were demanding a solution to their customers pleading for a Convenience, Safe Way to Order & Pay for their orders. It was a false alarm.
She ended up staying the course and not selecting Olo, again. That decision ultimately sealed her fate.
In the background, a friend of mine/CIO (Phil Crawford) that we had placed at Shake Shack (NYSE: SHAK) was interviewing for the role to replace her.
We coached him about what was happening at the brand and how we could help get the brand to where they needed to be from a digital POV.
When Phil Crawford joined on September 16, 2020, he had one goal: to build a frictionless guest experience and help CKE become digitally relevant within the QSR industry.
By November 15, 2020 -- we had a signed deal worth 8 figures across nearly 4 different modules: He trusted Olo and trusted best-in-class providers that we had helped him select behind the scenes to get BOD, Leadership & Franchisee Approval.
We didn't let him down. 18 months after his first day on the job, 85% of CKE’s 2,800 domestic restaurants are fully deployed with Olo and he was a hero within the brand.
The story is well documented and has led to more QSR brands including Jack in the Box to veer off their path and follow the nearly exact playbook that we designed for CKE.
And the best part? Remember that CIO who didn't select us back in 2016? She got hired on by an existing customer and went from being a detractor to a promoter and ignoring my emails to a text-message relationship :)”
📈 How to take action/learnings:
Build long-term relationships and look for ways to place champions at target accounts.
For large deals, patience is the new of the game and then strike (and go all in) when the time is right.
Oh and ‘Never, Ever, Ever F**kn Give up!’
Last but certainly not least, a war story from a good friend and the CEO/Founder of Replayz, Dave Kennet.
btw if you’re a Gong (or revenue intelligence) user and not using Replayz IQ to get the most out of your investment - you’re missing out.
Here’s a great win from early in Dave’s career:
“It was the year 2000. I was fresh out of University and had recently secured my first 'grown-up' role. I was Director of Business Development at a company called Worldid. No idea how I snagged this title. Best explanation is that it was the wild wild west of the Dot Com era. I got lucky.
At the time, Alibaba was our biggest competitor. They were #1 and we were #2. (Spoiler Alert- Alibaba won). We just held #2 position for a few months in the early days and then the gap from second place to market leader looked more like trying to chase a speed boat in a canoe....with one paddle.....in a winter storm.
My young innocence was a strength and a weakness.
We needed to find a creative way to get more traffic to our website. Funding was dwindling and revenue was not scaling the way we had hoped. I approached some major companies, that, frankly, most of our executives thought I had no business approaching. It was a David and Goliath-type scenario. But I didn't know any better, and thank goodness for that. I had one executive in my corner, our COO. He believed. And he encouraged me to think big. He told me to disregard the other execs and keep pounding the phones. We needed a Hail Mary.
He explained to me that the problem was that we needed our first Anchor partner. A strong brand that showed the rest of the market that a worthy, credible company believed in us. This was a new concept for me then.
I was trying to get meetings with The Times of London, Microsoft, Forbs, AOL & Yahoo. Each of these companies had solid traffic and captive users. Most weren't taking me seriously. Phone call after phone call and email after email, and I couldn't get a meeting. Until someone senior at the Times of London News UK Group appreciated my persistence and vision (+ the value for them) and somehow we snagged a meeting. "If you're willing to ACTUALLY fly out here, then sure, I'll assemble my fellow execs for a discussion."
The play was to have our marketplace cobranded in their business section, thus driving eyeballs to our marketplace. Our little Victoria, BC HQ'd start up with less than 20 employees were entering the big arena. Thanks to the mentorship of our amazing COO.
Our COO, President and this wet behind-the-ears 'Director of Biz Dev' (me) landed in London England to meet with the Online NewsUK Folks at the Times of London. The time came for our meeting. They held up their end of the bargain and they had the right people in the room. Somehow our message got across and before we knew it, they asked if they could take us to dinner as a thank you for us travelling all of that way to meet them.
Over dinner we learned that one of the senior leaders from The Times of London LOVED Kylie Minogue and had heard that Kylie was attending Boy George's Birthday Party at a prominent club close by. (crazy- I know!) Next thing you know, we made our way to that club, handed the Doorman a few extra bucks (awkward handshake with a mitt full of British Pounds after a frantic mission to the Bank Machine) and we were in the club. This DM from Linkedin from a few years ago will tell you what happened next.
We ended up getting that deal with the Times of London. We had a shot in the first place because we weren't afraid to think big and because I had a mentor who didn't let my spirits get dampened. The leadership folks at The Times of London told me much later that they felt aligned with our entrepreneurial spirit and they saw a good cultural fit. (who would have thunk it?!)
And guess what? After getting that anchor partnership in place, we ended up getting deals with most of the other big targets who wouldn't take our call. Anchor customers/partners are HUGE in the early days.
I hit up the 'ol Way Back Machine to grab a screenshot and give ya some proof.”
📈 How to take action/learnings:
Think Big. I've held myself back sometimes by not having the same naive innocence as my younger self.
Get a solid anchor customer. You just need one. That has helped me 'time after time'. (Cindy Lauper wasn't at the club).
Be like that COO and encourage young talent on my teams.
Of course, the power of face-to-face interactions will never get old. Would we have closed the deal without running into Kylie? Who knows?! (joking aside, they actually told me,'Kylie had nothing to do with our decision'...I'll choose to believe them:)
👀 More for your eyeballs:
Reid Hoffman talks AI with AI. The world is getting weird 🤯
👂More for your eardrums:
Want to know how Bob Elliot (3x CRO/SVP of Sales and Former MD at SAP) and his team grew one of their largest accounts to 53M in just 30 months? Bob breaks it all down in this week’s GTM pod.
🚀 Start-ups to watch:
A big Congrats to CloseFactor for Closing their Series A. “Built to harness the vast potential in automating manual research by employing machine learning techniques at scale, CloseFactor helps business-to-business sales and marketing teams identify the right target accounts to go after — including the right people at those accounts — so go-to-market teams have the blueprint to execute their strategy and hit their goals,” Joshi, founder, said. “Our goal is to become the go-to-marketing operating system for revenue teams.”
🔥Hottest GTM job of the week:
Head of Ecosystem Marketing at Mutiny, more details here.
See more top GTM jobs here.
—---------------------------------
Appreciate you all.
If you’re getting value from this newsletter, please share it with your friends and colleagues who are looking for some weekly GTM inspiration.
Happy Friday.
Barker.
✌️
Love Nipsey